Wes Kao's piece is a strong complement to the classic managing-up writing because it is more tactical and more operator-minded. The emphasis is on habits: how you communicate tradeoffs, how you surface risk early, how you reduce work for your manager, and how you build trust through consistency.
What makes it useful is that it does not romanticize the relationship. Managing up often means having conversations that feel risky, inconvenient, or awkward in the short term so the working relationship is stronger in the long term. Kao treats managing up as a craft that gets sharper with deliberate practice, not a personality trait you either have or lack.
Several of the principles center on reducing cognitive load for your manager. That means leading with the headline instead of the backstory, presenting options with a clear recommendation rather than an open-ended question, and flagging risks before they escalate. When you consistently make it easier for your manager to make good decisions, you earn the kind of trust that translates into more autonomy, better projects, and stronger advocacy when it counts. Kao also emphasizes that managing up is not the same as managing impressions. The goal is not to look good. The goal is to make the working relationship more effective by improving how information travels upward.
Another thread worth noting is accountability for communication style. Different managers absorb information differently. Some want a quick Slack message, others want a structured doc. Some prefer to be looped in early, others want to hear from you only when something needs a decision. Paying attention to those preferences and adapting is not submissiveness. It is professional fluency. Kao argues that ignoring your manager's communication preferences and then blaming them for not being receptive is a failure of managing up, not a failure of your manager.
Kao also addresses what to do when your manager is wrong or when you disagree with a direction. Kao does not suggest silent compliance. She suggests that you earn the right to push back by building a track record of reliable judgment and clear communication first. When you do push back, grounding your position in data, tradeoffs, and business impact makes the disagreement productive rather than personal. This is where practice matters most. Knowing you should raise a concern is different from having rehearsed the actual sentence you will say in the moment.
Key ideas to carry into practice
- Good managing up is proactive. It means surfacing constraints, tradeoffs, and uncertainty before they become surprises.
- Your manager usually does better when you bring judgment, not just raw updates. Lead with a recommendation, not a data dump.
- Trust compounds when your communication is clear, timely, and adapted to the way your manager works best.
- Reduce cognitive load by framing decisions as options with tradeoffs rather than open-ended questions.
- Adapt to your manager's preferred communication style instead of expecting them to adapt to yours.
- A lot of upward communication breaks down because people know the principle but have not practiced the actual sentence. Rehearsal closes the gap.
Common questions
Q: How do I bring a problem to my manager without sounding like I am just escalating noise?
A: Bring the problem with a point of view. For example: "We have two conflicting asks from product and sales. My recommendation is to prioritize the product launch dependency first because it affects a larger customer group. I want to sanity-check that with you before I communicate it." That is much stronger than a raw dump of frustration.
Q: What does good managing up sound like when I need clarity?
A: Ask for a decision in the form your manager can respond to quickly: "I see two viable paths. Here is the tradeoff between them. Which one do you want me to optimize for?" That reduces ambiguity and shows judgment.